Our invention relates to aryl oxabicyclooctane derivatives and phenyl norbornane derivatives defined according to the structures: ##STR4## wherein N is 1 or 2, processes for preparing same, perfumery uses thereof and intermediates used in said processes which intermediates are defined according to the structures: ##STR5## wherein M is 0, 1 or 2 and X is chloro or bromo.
Sweaty, animalic, amber, musky, dry camphoraceous and woody-peppery aromas, with green, herbaceous, sweaty, animalic, cigar box-like and woody topnotes are particularly desirable in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g., solid or liquid, anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations, cosmetic powders and perfumed polymers).
Compounds having the oxabicyclooctane nucleus have been known for use in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes for a number of years. Such compounds are disclosed in U.S. Pat. No. 4,269,862 and U.S. Pat. No. 5,087,707. Furthermore, Cineole is disclosed by Arctander "Perfume and Flavor Chemicals" (Aroma Chemicals) at Monograph 616 to have a eucalyptus aroma (its common name is "eucalyptol").
Nothing in the prior art however discloses the aryl oxabicyclooctane derivatives and phenyl norbornane derivatives of our invention for their organoleptic utilities.
However, Beilstein H6,591 (EIII6/2771) discloses the compound having the structure: ##STR6## prepared from Alpha-pinen oxide and alpha-campholenaldehyde. The Beilstein reference does not show that the compound can be further cyclized, however.
2-Phenyl-2-norbornene having the structure: ##STR7## (CAS 42114-13-6) is disclosed by Kropp, J.Amer.Chem.Soc., 1973, Vol. 95(14), pages 4611-19 [title: "Photochemistry of CycloAlkenes.VIII] 2-Phenyl-2-norbornene and 2-phenyl-2-bornene".
No disclosure of the use of the compound having the structure: ##STR8## in perfumery is disclosed. No disclosure of the mixture of the compounds having the structures: ##STR9## is disclosed in the prior art.